2,4-二氯苯氧乙酸壳寡糖酯的制备及抗菌活性研究
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摘要
以壳寡糖、2,4-二氯苯氧乙酸为原料,经壳寡糖氨基保护、2,4-二氯苯氧乙酸的羧基酰氯化、酰氯化后的2,4-二氯苯氧乙酸与壳寡糖羟基反应、脱除壳寡糖氨基保护最终得到2,4-二氯苯氧乙酸壳寡糖酯(Dcpo-O-COS)。通过傅里叶红外、紫外可见吸收、1 H核磁共振对2,4-二氯苯氧乙酸壳寡糖酯进行了结构表征,证明成功合成终产物。经X射线衍射仪、热分析仪、抗菌性研究测定,终产物的热稳定性、对大肠杆菌及金黄色葡萄球菌的抗菌性较原料壳寡糖有所提高。
The O-2,4-dichlorophenoxyacetic-oligochitosan(DcpoO-COS)was synthesized by chitosan oligosaccharide(COS)and 2,4-dichlorophenoxyacetic acid.The steps were as followed:amino protecting of chitosan oligosaccharide,carboxyl acyl chlorination of 2,4-dichlorophenoxyacetic acid,hydroxyl of COS reacted with acyl chlorination 2,4-dichlorophenoxyacetic acid,amino deprotection.Fourier transform infrared(FTIR),UV-Vis absorption and 1 H nuclear magnetic resonance(NMR)were used to characterize the structure of the final product.The results exhibited that Dcpo-O-COS was successfully synthesized.Moreover,both stability,tested by X-ray diffraction(XRD)and Thermogravimetric Analysis(TGA),and antibacterial activity,toresistance to Escherichia coli and Staphylococcus aureus,of Dcpo-O-COS were higher than COS.
The O-2,4-dichlorophenoxyacetic-oligochitosan(DcpoO-COS)was synthesized by chitosan oligosaccharide(COS)and 2,4-dichlorophenoxyacetic acid.The steps were as followed:amino protecting of chitosan oligosaccharide,carboxyl acyl chlorination of 2,4-dichlorophenoxyacetic acid,hydroxyl of COS reacted with acyl chlorination 2,4-dichlorophenoxyacetic acid,amino deprotection.Fourier transform infrared(FTIR),UV-Vis absorption and 1 H nuclear magnetic resonance(NMR)were used to characterize the structure of the final product.The results exhibited that Dcpo-O-COS was successfully synthesized.Moreover,both stability,tested by X-ray diffraction(XRD)and Thermogravimetric Analysis(TGA),and antibacterial activity,toresistance to Escherichia coli and Staphylococcus aureus,of Dcpo-O-COS were higher than COS.
引文
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[2]KONG M,CHEN X G,XING K,et al.Antimicrobial properties of chitosan and mode of action:A state of the art review[J].International Journal of Food Microbiology,2010,144(1):51-63.
[3]BADAWY M E I,RABEA E I,TAKTAK N E M,et al.The antibacterial activity of chitosan products blended with monoterpenes and their biofilms against plant pathogenic pacteria[J].Scientifica,2016,2 016:1-10.
[4]FENG Yong-wei,XIA Wen-shui.Preparation,characterization and antibacterial activity of water-soluble-fumaryl-chitosan[J].Carbohydrate Polymers,2011,83(3):1 169-1 173.
[5]VERLEE A,MINCKE S,STEVENS C V.Recent developments in antibacterial and antifungal chitosan and its derivatives[J].Carbohydr Polym,2017,164:268-283.
[6]YUE Lin,LI Jing-ru,CHEN Wan-wen,et al.Geraniol grafted chitosan oligosaccharide as a potential antibacterial agent[J].Carbohydrate Polymers,2017,176:356-364.
[7]LIU Xiao-li,JIANG Qi-xing,XIA Wen-shui.One-step procedure for enhancing the antibacterial and antioxidant properties of a polysaccharide polymer:Kojic acid grafted onto chitosan[J].International Journal of Biological Macromolecules,2018,113:1 125-1 133.
[8]LIU Xiao-li,XIA Wen-shui,JIANG Qi-xing,et al.Synthesis,characterization,and antimicrobial activity of kojic acid grafted chitosan oligosaccharide[J].Journal of Agricultural&Food Chemistry,2014,62(1):297-303.
[9]KHAN I,ULLAH S,OH D H.Chitosan grafted monomethyl fumaric acid as a potential food preservative[J].Carbohydrate Polymers,2016,152:87-96.
[10]WANG Zhao-dong,ZHENG Liu-chun,LI Chun-cheng,et al.Modification of chitosan with monomethyl fumaric acid in an ionic liquid solution[J].Carbohydrate Polymers,2015,117:973-979.
[11]LIU Jun,WEN Xiao-yuan,LU Jian-feng,et al.Free radical mediated grafting of chitosan with caffeic and ferulic acids:structures and antioxidant activity[J].International Journal of Biological Macromolecules,2014,65(5):97-106.
[12]XIE Min-hao,HU Bing,WANG Yan,et al.Grafting of gallic acid onto chitosan enhances antioxidant activities and alters rheological properties of the copolymer[J].Journal of Agricultural&Food Chemistry,2014,62(37):9 128-9 136.
[13]RUIZ-CARO R,VEIGA M D,MEO C D,et al.Mechanical and drug delivery properties of a chitosantartaric acid hydrogel suitable for biomedical applications[J].Journal of Applied Polymer Science,2011,123(2):842-849.
[14]REN Jian-ming,LI Qing,DONG Fang,et al.Phenolic antioxidants-functionalized quaternized chitosan:Synthesis and antioxidant properties[J].International Journal of Biological Macromolecules,2013,53(2):77-81.
[15]冯永巍,夏文水,申丽丽,等.O-苯甲酰壳聚糖的合成及其抑真菌活性[J].食品与生物技术学报,2011,30(3):367-370.
[16]王爱勤,俞贤达.烷基化壳聚糖衍生物的制备与性能研究[J].功能高分子学报,1998(1):83-86.
[17]李莹,周晓晶,王尉,等.防腐剂2,4-二氯苯氧乙酸标准物质研制[J].分析试验室,2015,34(11):1 306-1 310.
[18]刘蕊,李德红,李玲.2,4-二氯苯氧乙酸的研究进展[J].生命科学研究,2004(S2):71-75.
[19]黄丽.2,4-D-明胶/壳聚糖/葡甘聚糖复合微球的制备及其性能[J].皮革科学与工程,2008,18(6):27-31.
[20]KURITA K,AKAO H,YANG J,et al.Nonnatural branched polysaccharides:Synthesis and properties of chitin and chitosan havingα-mannoside branches[J].Macromolecules,1998,31(15):4 764-4 769.
[21]冯永巍.壳聚糖的化学改性及其衍生物的抑菌活性研究[D].无锡:江南大学,2011:24.
[22]LI Cong-xin,GUO Tian-ying,ZHOU De-zhong,et al.Anovel glutathione modified chitosan conjugate for efficient gene delivery[J].Journal of Controlled Release,2011,154(2):177-188.
[23]VERHEUL R J,AMIDI M,VAN D W S,et al.Synthesis,characterization and in vitro biological properties of-methyl free,-trimethylated chitosan[J].Biomaterials,2008,29(27):3 642-3 649.
[24]董炎明,毕丹霞,赵雅青,等.十一种壳聚糖衍生物的紫外吸收特性[J].应用化学,2005,22(10):1 050-1 054.
[25]刘晓丽.壳寡糖-曲酸衍生物的制备及其抗菌活性研究[D].无锡:江南大学,2015:18-23.
[26]BOZIC M,GORGIEVA S,KOKOL V.Laccase-mediated functionalization of chitosan by caffeic and gallic acids for modulating antioxidant and antimicrobial properties[J].Carbohydrate Polymers,2012,87(4):2 388-2 398.
[27]NIU Xu-feng,LIU Zhong-ning,HU Jiang,et al.Microspheres Assembled from Chitosan-Graft-Poly(lactic acid)Micelle-Like Core-Shell Nanospheres for Distinctly Controlled Release of Hydrophobic and Hydrophilic Biomolecules[J].Macromolecular Bioscience,2016,16(7):1 039-1 047.
[28]WORANUCH S,YOKSAN R,AKASHI M.Ferulic acidcoupled chitosan:Thermal stability and utilization as an antioxidant for biodegradable active packaging film[J].Carbohydrate Polymers,2015,115:744-751.
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